If you’re a fan of the classic 1998 rom-com “You’ve Got Mail” starring Tom Hanks and Meg Ryan, you’ll love these 15 similar feel-good movies filled with witty dialogue, unlikely romances, and plenty of heart. From 90s favorites to more recent flicks, these films are perfect for date night or whenever you need a dose of lighthearted escapism. Let’s dive in!
1. Sleepless in Seattle (1993)
Directed by Nora Ephron
Starring Tom Hanks, Meg Ryan, Bill Pullman, Ross Malinger
This earlier pairing of Hanks and Ryan is a must-watch for any rom-com lover. The story follows Sam Baldwin (Hanks), a recently widowed father who moves to Seattle with his young son Jonah (Malinger). When Jonah calls into a radio talk show looking for a new wife for his dad, Sam reluctantly gets on the line and shares his story. His heartfelt words captivate listeners across the country, including journalist Annie Reed (Ryan) in Baltimore.
Despite being engaged, Annie becomes infatuated with Sam’s story and impulsively writes him a letter suggesting they meet atop the Empire State Building on Valentine’s Day. Meanwhile, Sam has started dating a woman in Seattle, unaware of Annie’s existence. Jonah is determined to get his dad and Annie together, setting the stage for a fateful meeting.
The film’s success cemented Hanks and Ryan as the king and queen of romantic comedies in the 90s. With its clever references to An Affair to Remember, witty dialogue, and exploration of finding love again after loss, Sleepless is a timeless classic.
2. While You Were Sleeping (1995)
Directed by Jon Turteltaub
Starring Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle, Jack Warden
This charming rom-com stars Sandra Bullock as Lucy, a lonely Chicago Transit Authority token collector who saves the life of her crush, Peter (Gallagher), after he’s mugged and falls onto the train tracks. At the hospital, a misunderstanding leads Peter’s family to believe Lucy is his fiancée. She goes along with it, enjoying the feeling of finally belonging to a family. But things get complicated when she starts falling for Peter’s brother Jack (Pullman).
While You Were Sleeping was praised for its warmth, humor, and Bullock’s endearing performance. It’s the perfect cozy movie to watch around the holidays with its Christmas and New Year’s Eve scenes. The family dynamics are relatable and heartfelt, and the chemistry between Bullock and Pullman is undeniable.
3. Serendipity (2001)
Directed by Peter Chelsom
Starring John Cusack, Kate Beckinsale, Jeremy Piven, Molly Shannon
This whimsical romance follows two strangers, Jonathan (Cusack) and Sara (Beckinsale), who meet by chance while Christmas shopping at Bloomingdale’s in New York City. Despite feeling an instant connection, they go their separate ways, leaving their future up to fate. Years later, on the eve of their respective weddings to other people, both Jonathan and Sara can’t stop thinking about that magical night. They set off on a quest to find each other again, leading to near-misses and surprises in both NYC and San Francisco.
Serendipity is all about trusting in destiny and taking chances on love. Cusack and Beckinsale have great onscreen chemistry, and the film’s whimsical tone sets it apart from other rom-coms. With memorable scenes at iconic NYC locations like Serendipity 3 cafe and the Waldorf Astoria hotel, it’s a love letter to the city and the role of chance in our lives.
4. When Harry Met Sally (1989)
Directed by Rob Reiner
Starring Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Can men and women ever really be “just friends”? That’s the central question of this iconic rom-com written by Nora Ephron. Harry (Crystal) and Sally (Ryan) meet by chance when they share a car ride from Chicago to New York after graduating college. They don’t exactly hit it off, but over the next 12 years they keep running into each other, slowly forming a deep friendship. Their other friends Marie (Fisher) and Jess (Kirby) are convinced Harry and Sally are perfect for each other, but they insist romance would ruin everything.
When Harry Met Sally is a hilarious and heartfelt look at love, friendship, and everything in between. Crystal and Ryan have electric chemistry, and their characters’ long history feels authentic. Ephron’s Oscar-nominated script is full of endlessly quotable lines, and the film’s fake-orgasm-in-a-deli scene is one of the most famous in rom-com history.
5. Notting Hill (1999)
Directed by Roger Michell
Starring Julia Roberts, Hugh Grant, Rhys Ifans, Emma Chambers
This charming British rom-com stars Grant as Will, the owner of a struggling travel bookshop in London’s Notting Hill neighborhood. One day, famous American actress Anna Scott (Roberts) comes in to browse and ends up buying a book. Sparks fly between the two, but their very different lifestyles make romance complicated. As their relationship develops, they must navigate the challenges of fame and decide what really matters.
Notting Hill offers a lovely slice of life in a picturesque London neighborhood. Grant and Roberts are both at the top of their rom-com games, and their chemistry is undeniable. Ifans provides comic relief as Will’s eccentric flatmate Spike. The film’s message about looking past someone’s public persona to connect with the real person underneath still resonates. A huge hit,
6. 10 Things I Hate About You (1999)
Directed by Gil Junger
Starring Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
This modernized retelling of Shakespeare’s The Taming of the Shrew follows the romance between fiery feminist Kat Stratford (Stiles) and charming bad boy Patrick Verona (Ledger) at a Seattle high school. Kat’s younger sister Bianca (Oleynik) is eager to start dating, but their overprotective dad won’t let her until Kat has a boyfriend too. New student Cameron (Gordon-Levitt) has a crush on Bianca, so he arranges for Patrick to woo the seemingly un-dateable Kat. Unexpected feelings develop as they verbally spar and challenge each other’s defenses.
10 Things I Hate About You launched the careers of its young stars and remains a teen movie classic. Ledger is magnetic in his breakout role, and his chemistry with Stiles sizzles. The script is sharp and funny, with plenty of clever nods to its Shakespearean source material.
7. Never Been Kissed (1999)
Directed by Raja Gosnell
Starring Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski
Barrymore stars as Josie Geller, an insecure 25-year-old copy editor who gets the chance to prove herself as a reporter when she’s assigned to go undercover at a high school. Having been a nerdy outcast during her own teen years, Josie is determined to do things differently this time around. With the help of her popular younger brother Rob (Arquette), she infiltrates the cool crowd. But Josie’s growing feelings for her English teacher Sam (Vartan) make things complicated, especially when he thinks she’s a student.
Never Been Kissed is a sweet, funny look at getting a second chance to live out your high school dreams. Barrymore is endearing as the awkward Josie, and Arquette provides great comic support as her exasperated brother. The film’s message about staying true to yourself and not worrying so much what others think is a valuable one.
8. 13 Going on 30 (2004)
Directed by Gary Winick
Starring Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
Garner stars as Jenna Rink, a gawky 13-year-old in 1987 who makes a wish on her birthday to be “thirty, flirty, and thriving.” She wakes up the next day as her 30-year-old self (Garner) in 2004, with no memory of the intervening 17 years. Jenna discovers she’s now a successful magazine editor with a fabulous NYC apartment. . . but she may have lost touch with what really matters, including her childhood best friend Matt (Ruffalo). As Jenna navigates her new life, she realizes some things are more important than popularity.
13 Going on 30 is a fun, nostalgic comedy with a touching message about staying true to yourself. Garner is delightful in the lead role, perfectly capturing the spirit of a teen in a grown woman’s body. Her chemistry with Ruffalo is sweet and genuine. The 80s flashback scenes are a blast, with great music and fashion choices.
9. Music and Lyrics (2007)
Directed by Marc Lawrence
Starring Hugh Grant, Drew Barrymore, Brad Garrett, Kristen Johnston
Grant stars as Alex Fletcher, a washed-up 80s pop star who gets a chance at a comeback when a current diva asks him to write a song for her. The only problem is Alex hasn’t written a hit in years and has severe writer’s block. Enter Sophie Fisher (Barrymore), the woman who waters his plants. Sophie has a way with words, and the two soon form a songwriting partnership. Creative and romantic sparks fly as they race to finish the song before the deadline.
Music and Lyrics is a charming, underrated gem that reunites Grant and Barrymore after Never Been Kissed. The two have wonderful chemistry, and Grant is hilarious as the self-deprecating former pop star. The film’s original songs are actually quite catchy, especially the 80s-style “Pop Goes My Heart.”
10. The Holiday (2006)
Directed by Nancy Meyers
Starring Cameron Diaz, Kate Winslet, Jude Law, Jack Black
This cozy Christmas rom-com follows two unlucky-in-love women who swap homes for the holidays. Amanda (Diaz) is a workaholic movie trailer editor in Los Angeles, while Iris (Winslet) is a wedding columnist in a quaint English village. Both are reeling from bad breakups and in need of a change of scenery. After connecting online, they agree to swap houses for two weeks. In England, Amanda meets Iris’ charming brother Graham (Law). Back in California, Iris befriends her elderly neighbor Arthur (Eli Wallach) and starts falling for film composer Miles (Black).
The Holiday is the perfect movie to watch curled up by the fire with a mug of hot cocoa. Diaz and Winslet are both endearing in their “fish out of water” roles, and Law and Black make for swoonworthy love interests. The film’s picturesque locations will have you wanting to book your own home exchange. Meyers’ script strikes a nice balance between humor and heart.
11. 27 Dresses (2008)
Directed by Anne Fletcher
Starring Katherine Heigl, James Marsden, Malin Akerman, Judy Greer
Heigl stars as Jane, a perpetual bridesmaid who’s been in 27 weddings and secretly carries a torch for her boss George (Edward Burns). When George falls for Jane’s younger sister Tess (Akerman), Jane is once again asked to be a bridesmaid. To make matters worse, Jane’s “always a bridesmaid” story catches the eye of cynical wedding reporter Kevin (Marsden), who sees her as his ticket to a big promotion. As Jane and Kevin spend more time together, they start to develop real feelings that could throw a wrench in all their plans.
27 Dresses is a fun, frothy rom-com anchored by Heigl and Marsden’s winning chemistry. Heigl is relatable as the selfless Jane who always puts others’ needs before her own, and Marsden is charming as the guy who helps her start prioritizing her own happiness. Akerman is also great as the self-absorbed Tess. The film’s message about not waiting around for someone to notice you is an important one.
12. Definitely, Maybe (2008)
Directed by Adam Brooks
Starring Ryan Reynolds, Isla Fisher, Derek Luke, Abigail Breslin
Reynolds stars as Will Hayes, a soon-to-be-divorced dad who tells his young daughter Maya (Breslin) the story of how he met her mother. Will changes the names so Maya has to guess which of the three women from his past is “the one.” Is it his college sweetheart Emily (Elizabeth Banks)? Apolitical campaign worker April (Fisher)? Or ambitious journalist Summer (Rachel Weisz)? As Will revisits his romantic history, he starts to question his belief in soulmates and happy endings.
Definitely, Maybe is a sweet, refreshingly grounded rom-com. Reynolds is charming as always, and he has great chemistry with all three of his leading ladies. Fisher is especially winning as April, the free spirit who challenges Will’s worldview. The film’s 90s setting is fun without being gimmicky, and the framing device with Maya is genuinely heartwarming.
13. (500) Days of Summer (2009)
Directed by Marc Webb
Starring Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend, Chloe Grace Moretz
This quirky anti-rom-com follows the 500-day relationship between hopeless romantic Tom (Gordon-Levitt) and the commitment-phobic Summer (Deschanel). Tom falls head over heels for Summer, but she insists she doesn’t believe in true love and just wants to keep things casual. The film jumps back and forth in time, showing the highs and lows of their relationship out of order. As Tom tries to win Summer over, he starts to question everything he thought he knew about love and destiny.
(500) Days of Summer is a clever, unconventional look at modern romance. Gordon-Levitt and Deschanel have electric chemistry, and their characters feel like real, flawed people you could know in real life. The nonlinear structure keeps you guessing, and the film’s frank exploration of heartbreak and disillusionment is refreshingly honest.
14. Crazy, Stupid, Love (2011)
Directed by Glenn Ficarra, John Requa
Starring Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone
This ensemble comedy follows three interconnected storylines. Cal (Carell) is blindsided when his high school sweetheart Emily (Moore) asks for a divorce. Determined to get his groove back, he starts hanging out at a trendy bar, where he meets smooth ladies’ man Jacob (Gosling). Jacob takes Cal under his wing and helps him rediscover his manhood. Meanwhile, Cal’s son Robbie (Jonah Bobo) is nursing a crush on his babysitter Jessica (Analeigh Tipton), who’s infatuated with Cal. And Jacob starts to question his playboy lifestyle when he falls for Hannah (Stone), a strong-willed law student.
Crazy, Stupid, Love is a hilarious and heartfelt look at love at all ages. The all-star cast is fantastic, with Carell and Gosling displaying wonderful odd-couple chemistry. Moore brings depth to what could have been a one-note character, and Stone is luminous as always. The film’s interweaving storylines come together in surprising and satisfying ways.
15. To All the Boys I’ve Loved Before (2018)
Directed by Susan Johnson
Starring Lana Condor, Noah Centineo, Janel Parrish, Anna Cathcart
Based on the popular YA novel, this Netflix rom-com follows shy high schooler Lara Jean Covey (Condor). Whenever Lara Jean has an intense crush, she writes the boy a love letter she never intends to send, pouring out her feelings so she can move on. But when the letters accidentally get mailed, Lara Jean finds her love life spinning out of control. To convince her sister’s ex-boyfriend Josh (Israel Broussard) that she’s over him, Lara Jean starts fake-dating popular jock Peter Kavinsky (Centineo). But as they spend more time together, real feelings start to develop.
To All the Boys I’ve Loved Before is a sweet, sincere teen rom-com that became a surprise hit for Netflix. Condor is endearing as the awkward Lara Jean, and Centineo became an overnight heartthrob as Peter. The film’s depiction of a biracial family feels authentic and groundbreaking for the genre. With its focus on sisterhood, growing up, and being true to yourself, the film has resonated with viewers of all ages.
These 15 films all capture the charm, humor, and heart of You’ve Got Mail in their own unique ways. Whether you’re in the mood for a 90s classic, a quirky indie, or a modern Netflix favorite, you’re sure to find a rom-com on this list to make you laugh, cry, and believe in love again. So grab some popcorn, settle in, and get ready to fall head over heels for these delightful films.
